Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
5 Bedroom Homes in Chester, NY
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

12 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
3 bedsNew constructionWith a pool

5 Bedroom Homes in Chester, NY

5 Bedroom Homes in Chester, NY

Hide Map
12 Listings
Map

5 Bedroom Homes in Chester, NY

12 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 700 Atateka Drive — photoNew43Active

    $499,900

    5 bd · 3 ba · 1,646 sqft

    700 Atateka Drive, Chester, NY

    Michael J Lynch · Coldwell Banker Prime Properties

  2. 65 Oxford Springs Road — photo38Active

    $699,000

    5 bd · 4 ba · 3,463 sqft

    65 Oxford Springs Road, Chester, NY

    Stephanie Dolan · HomeSmart Homes & Estates

  3. 3 Hilltop Lane — photo1Active

    $750,000

    5 bd · 3 ba · 2,700 sqft

    3 Hilltop Lane, Chester, NY

    Moshe Kaufman · MK Realty Inc

  4. 1 Hilltop Lane — photo1Active

    $750,000

    5 bd · 3 ba · 2,700 sqft

    1 Hilltop Lane, Chester, NY

    Moshe Kaufman · MK Realty Inc

  5. 20 Vetter Avenue — photoPrice Reduced28Active

    $320,000

    5 bd · 2 ba · 1,286 sqft

    20 Vetter Avenue, Chester, NY

    Julia Pucciarelli · Gallo Realty ADK Inc

  6. 190 Kingsley Ln Ext — photoPrice Reduced56Active

    $899,000

    5 bd · 3 ba · 2,482 sqft

    190 Kingsley Ln Ext, Chester, NY

    Brooke Clark · Four Seasons Sothebys International Realty

  7. 2 Hemlock Court — photo3Active

    $750,000

    5 bd · 3 ba · 2,700 sqft

    2 Hemlock Court, Chester, NY

    Moshe Kaufman · MK Realty Inc

  8. 5 Hilltop Lane — photo5Active

    $850,000

    5 bd · 3 ba · 3,200 sqft

    5 Hilltop Lane, Chester, NY

    Moshe Kaufman · MK Realty Inc

  9. 19 Grand View Terrace — photo37Active

    $789,900

    5 bd · 4 ba · 4,697 sqft

    19 Grand View Terrace, Chester, NY

    Randolph Rogers · eXp Realty

  10. 2 Garnett Hill Road — photo35Active

    $999,999

    5 bd · 3 ba · 4,772 sqft

    2 Garnett Hill Road, Chester, NY

    Rachel L Baruchov · Platinum Realty Associates

  11. 53 Gibson Hill Road — photo48Active

    $1,100,000

    5 bd · 4 ba · 5,312 sqft

    53 Gibson Hill Road, Chester, NY

    Ammar Iqbal · eXp Realty

  12. 12 Damian Court — photoPrice Reduced34Active

    $949,000

    5 bd · 4 ba · 3,136 sqft

    12 Damian Court, Chester, NY

    Elimelech Kremer · MS Realty Group USA, Inc

Explore Chester homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
  • Co-ops

By feature

Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

Global MLS
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Information is deemed reliable but not guaranteed.
Listing information ©2026 Local REALTOR® - Douglas Perlson, Corp. Broker - (646) 315-9116. All Rights Reserved. Last Updated: 2026-09-20 00:39:50 UTC
OneKey MLS
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Chester, NY community profile

    Population
    4,099
    Median income
    $110,682
    Housing units
    1,761
    People per sq. mi.
    120.2
    Area
    34.1 sq. mi.

    Source: HJN community data

    Chester housing market

    August 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 13 sales · as of Aug 28, 2026

    Homes on the market · MLS, as of Aug 24, 2026–Aug 28, 2026

    Median list price
    $699,998
    Homes for sale
    74
    Median days on market
    41 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

    Median home size
    2,097 sq. ft.